新的1,2,3-苯并三唑基硫脲类似物：合成、α -葡萄糖苷酶、脲酶活性及分子对接研究

IF 2.218 Q2 Chemistry

Chemical Data Collections Pub Date : 2025-01-28 DOI:10.1016/j.cdc.2025.101185

Urooba Khan , Shawkat Hayat , Muhammad Nabi , Hayat Ullah , Ali Umar , Muhammad Saleem Khan , Fazal Rahim , Muhammad Azam Khan , Rashid Iqbal , Farzana Gul , Muhammed Perviaz

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引用次数: 0

摘要

合成了基于苯并三唑的硫脲类似物（1-13），通过1H-NMR、13C-NMR和HREI-MS等不同技术对其进行了表征，并对α -葡萄糖苷酶和脲酶进行了评价。所有合成的类似物均表现出不同的抑制电位，与标准药物阿卡波糖（IC50 = 12.30±1.10µM）相比，对α-葡萄糖苷酶的IC50值为2.30±0.10 ~ 19.40±0.20µM；与标准药物硫脲（IC50 = 19.20±0.21µM）相比，对脲酶的IC50值为8.50±0.30 ~ 27.60±0.40µM。在α-葡萄糖苷酶方面，类似物12 （IC50 = 2.30±0.10µM）的活性比标准药物阿卡波糖高数倍；在脲酶方面，类似物7 （IC50 = 8.50±0.30µM）的活性比标准药物硫脲高数倍。模拟物13在两种情况下都显示出最少的活性。我们进行了分子对接研究，以证明最活跃的支架与酶的活性位点的结合相互作用。所有化合物均对3T3小鼠成纤维细胞系具有细胞毒性，检测为无毒。

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New 1,2,3-Benzotriazole-based thiourea analogues: Synthesis, alpha-glucosidase, urease activities and molecular docking study

-Benzotriazole-based thiourea analogues (1–13) were synthesized, characterized through different techniques such as ¹H-NMR, ¹³C-NMR, and HREI-MS, and evaluated against alpha-glucosidase and urease enzymes. All synthesized analogues exhibited variable inhibitory potential, with IC₅₀ values ranging from 2.30 ± 0.10 to 19.40 ± 0.20 µM (against α-glucosidase) as compared to standard drug acarbose (IC₅₀ = 12.30 ± 1.10 µM) and 8.50 ± 0.30 to 27.60 ± 0.40 µM (against urease) as compared to standard drug thiourea (IC₅₀ = 19.20 ± 0.21 µM). In case of α-glucosidase, analogues 12 (IC₅₀ = 2.30 ± 0.10 µM) exhibited many times better activity than standard drug acarbose, while in case of urease, compounds 7 (IC₅₀ = 8.50 ± 0.30 µM) showed many times better activity than standard drug thiourea. Analogue 13 showed the least activity in both cases. We performed molecular docking studies to demonstrate the binding interaction of the most active scaffolds with the enzyme's active site. All compounds were verified for cytotoxicity against the 3T3 mouse fibroblast cell line and detected as non-toxic.

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来源期刊

Chemical Data Collections Chemistry-Chemistry (all)

CiteScore

6.10

自引率

0.00%

发文量

169

审稿时长

24 days

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